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In most online dictionaries, if you look up 居る, it gives you two readings: いる, formerly ゐる, and おる, formerly をる.

However, I can't tell what the difference in connotation or usage would be. I couldn't find too many resources or articles talking about this.

Wiktionary states the following etymology:

Listed in some sources as derived from the 連用形 (ren'yōkei, “continuative or stem form”) wi of verb wiru (modern いる (iru)) + ある (aru). The conjugation paradigm for woru is indeed the same as aru for Classical and Old Japanese. However, the resulting compounded *wiaru form would ordinarily become yaru or eru via historical phonetic change, and the vowel shift to /o/ is unexplainable in this hypothesis.

Wiktionary also states basically the same definitions for both the verbs いる and おる.

いる:

[verb] (of animate objects) to exist, to be

[verb] (of animate objects) to have

おる:

[verb] (of animate objects) to exist, to be, to have

So what's the difference in usage between いる and おる? Is formality all there is to it? Or is there other differences? When should one use おる instead of いる?

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Have you ever learned about keigo? The first thing you have to learn about おる is that it's the humble equivalent of いる, just like いらっしゃる is the honorific equivalent of いる. This is something explained in a grammar textbook rather than a word-based Japanese-English dictionary.

After learning that, there are two important exceptions regarding おる:

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